{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,5]],"date-time":"2026-07-05T19:24:09Z","timestamp":1783279449100,"version":"3.54.6"},"reference-count":82,"publisher":"Royal Society of Chemistry (RSC)","issue":"47","license":[{"start":{"date-parts":[[2022,10,27]],"date-time":"2022-10-27T00:00:00Z","timestamp":1666828800000},"content-version":"vor","delay-in-days":299,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/3.0\/"}],"funder":[{"DOI":"10.13039\/501100001845","name":"Science for Equity, Empowerment and Development Division","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001845","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["rsc.org"],"crossmark-restriction":true},"short-container-title":["RSC Adv."],"abstract":"<jats:p>A catalyst-free methylenation of 7-aza indoles under MW irradiation and CAN oxidation of methylenated products to the respective ketones are achieved. Plausible mechanisms of the reactions and photophysical properties of the products are described.<\/jats:p>","DOI":"10.1039\/d2ra05849a","type":"journal-article","created":{"date-parts":[[2022,10,27]],"date-time":"2022-10-27T05:11:22Z","timestamp":1666847482000},"page":"30712-30721","update-policy":"https:\/\/doi.org\/10.1039\/rsc_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Synthesis of 5-aryl-3,3\u2032-bis-indolyl and bis-7-aza-indolyl methanone derivatives from 5-bromo-7-azaindoles\n                    <i>via<\/i>\n                    sequential methylenation using microwave irradiation, CAN oxidation, and Suzuki coupling reactions"],"prefix":"10.1039","volume":"12","author":[{"given":"Elavarasan","family":"Pavithra","sequence":"first","affiliation":[{"name":"Department of Chemistry, School of Advanced Sciences, VIT, Vellore-632014, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5108-9303","authenticated-orcid":false,"given":"Sathananthan","family":"Kannadasan","sequence":"additional","affiliation":[{"name":"Department of Chemistry, School of Advanced Sciences, VIT, Vellore-632014, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0411-1982","authenticated-orcid":false,"given":"Ponnusamy","family":"Shanmugam","sequence":"additional","affiliation":[{"name":"Organic and Bioorganic Chemistry Division, CSIR-Central Leather Research Institute (CLRI), Adyar, Chennai-600020, India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"292","published-online":{"date-parts":[[2022]]},"reference":[{"key":"D2RA05849A\/cit1\/1","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1039\/D0QO01079K","volume":"8","author":"Motati","year":"2021","journal-title":"Org. Chem. Front."},{"key":"D2RA05849A\/cit2\/1","doi-asserted-by":"crossref","first-page":"3142","DOI":"10.1039\/c001897j","volume":"39","author":"Zhao","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"D2RA05849A\/cit3a\/1","doi-asserted-by":"crossref","first-page":"3405","DOI":"10.1002\/chem.201803642","volume":"25","author":"Chen","year":"2019","journal-title":"Chem.\u2013Eur. J."},{"key":"D2RA05849A\/cit3b\/1","doi-asserted-by":"crossref","first-page":"14030","DOI":"10.1002\/chem.201301555","volume":"19","author":"Sun","year":"2013","journal-title":"Chem.\u2013Eur. J."},{"key":"D2RA05849A\/cit3c\/1","doi-asserted-by":"crossref","first-page":"2664","DOI":"10.1002\/asia.201800766","volume":"13","author":"Qiao","year":"2018","journal-title":"Chem.\u2013Asian J."},{"key":"D2RA05849A\/cit3d\/1","first-page":"2031","volume":"19","author":"Ha","year":"2018","journal-title":"Synlett"},{"key":"D2RA05849A\/cit3e\/1","doi-asserted-by":"crossref","first-page":"7564","DOI":"10.1039\/D0RA10413B","volume":"11","author":"Elagawany","year":"2021","journal-title":"RSC Adv."},{"key":"D2RA05849A\/cit4a\/1","doi-asserted-by":"crossref","first-page":"150974","DOI":"10.1016\/j.tetlet.2019.150974","volume":"60","author":"Lee","year":"2019","journal-title":"Tetrahedron Lett."},{"key":"D2RA05849A\/cit4b\/1","doi-asserted-by":"crossref","first-page":"3024","DOI":"10.1002\/slct.201800060","volume":"3","author":"Halimehjani","year":"2018","journal-title":"ChemistrySelect"},{"key":"D2RA05849A\/cit5a\/1","doi-asserted-by":"crossref","first-page":"615","DOI":"10.1055\/s-0032-1318172","volume":"45","author":"Han","year":"2013","journal-title":"Synthesis"},{"key":"D2RA05849A\/cit5b\/1","doi-asserted-by":"crossref","first-page":"4007","DOI":"10.1055\/s-0036-1590881","volume":"49","author":"Hu","year":"2017","journal-title":"Synthesis"},{"key":"D2RA05849A\/cit5c\/1","doi-asserted-by":"crossref","first-page":"17620","DOI":"10.1039\/C9NJ01486A","volume":"43","author":"Maurya","year":"2019","journal-title":"New J. Chem."},{"key":"D2RA05849A\/cit5d\/1","doi-asserted-by":"crossref","first-page":"9763","DOI":"10.1016\/j.tet.2012.09.028","volume":"68","author":"Parida","year":"2012","journal-title":"Tetrahedron"},{"key":"D2RA05849A\/cit5e\/1","doi-asserted-by":"crossref","first-page":"61","DOI":"10.15227\/orgsyn.018.0061","volume":"18","author":"Lieberman","year":"1938","journal-title":"Org. Synth."},{"key":"D2RA05849A\/cit5f\/1","doi-asserted-by":"crossref","first-page":"58","DOI":"10.15227\/orgsyn.036.0058","volume":"36","author":"Nishimura","year":"1956","journal-title":"Org. Synth."},{"key":"D2RA05849A\/cit5g\/1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1021\/cr50019a001","volume":"58","author":"Hartford","year":"1958","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit5h\/1","doi-asserted-by":"crossref","first-page":"4176","DOI":"10.1021\/jo01275a036","volume":"33","author":"Vlattas","year":"1968","journal-title":"J. Org. Chem."},{"key":"D2RA05849A\/cit5i\/1","doi-asserted-by":"crossref","first-page":"1085","DOI":"10.1021\/ja01210a050","volume":"68","author":"Marvel","year":"1946","journal-title":"J. Am. Chem. Soc."},{"key":"D2RA05849A\/cit5j\/1","doi-asserted-by":"crossref","first-page":"586","DOI":"10.1021\/jo01144a011","volume":"16","author":"Carpenter","year":"1951","journal-title":"J. Org. Chem."},{"key":"D2RA05849A\/cit5k\/1","doi-asserted-by":"crossref","first-page":"4493","DOI":"10.1016\/S0040-4039(00)70065-7","volume":"7","author":"Syper","year":"1966","journal-title":"Tetrahedron Lett."},{"key":"D2RA05849A\/cit5l\/1","doi-asserted-by":"crossref","first-page":"2033","DOI":"10.1021\/jo01344a544","volume":"31","author":"Trahanovsky","year":"1966","journal-title":"J. Org. Chem."},{"key":"D2RA05849A\/cit5m\/1","doi-asserted-by":"crossref","first-page":"1689","DOI":"10.1021\/ja01589a055","volume":"78","author":"Gilman","year":"1956","journal-title":"J. Am. Chem. Soc."},{"key":"D2RA05849A\/cit5n\/1","doi-asserted-by":"crossref","first-page":"3149","DOI":"10.1080\/00397919508015465","volume":"25","author":"Ganin","year":"1995","journal-title":"Synth. Commun."},{"key":"D2RA05849A\/cit5o\/1","doi-asserted-by":"crossref","first-page":"2769","DOI":"10.1055\/s-2005-917118","volume":"18","author":"Hosseinzadeh","year":"2005","journal-title":"Synlett"},{"key":"D2RA05849A\/cit5p\/1","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/j.apcata.2007.09.021","volume":"333","author":"Ghaffarzadeh","year":"2007","journal-title":"Appl. Catal., A"},{"key":"D2RA05849A\/cit6a\/1","doi-asserted-by":"crossref","first-page":"10928","DOI":"10.3390\/molecules200610928","volume":"20","author":"Tobiszewski","year":"2015","journal-title":"Molecules"},{"key":"D2RA05849A\/cit6b\/1","doi-asserted-by":"crossref","first-page":"2169","DOI":"10.1021\/cr078380v","volume":"107","author":"Horvath","year":"2007","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit6c\/1","doi-asserted-by":"crossref","DOI":"10.5772\/68007","volume-title":"Green Chemistry","author":"Saleh","year":"2018","unstructured":"H. E. D. M.Saleh , and  M.Koller , in  Green Chemistry ,  IntechOpen ,  2018"},{"key":"D2RA05849A\/cit6d\/1","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1016\/j.gresc.2021.05.001","volume":"2","author":"Zhang","year":"2021","journal-title":"Green Synthesis and Catalysis"},{"key":"D2RA05849A\/cit6e\/1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.gresc.2020.06.002","volume":"1","author":"Kim","year":"2020","journal-title":"Green Synthesis and Catalysis"},{"key":"D2RA05849A\/cit6f\/1","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1039\/B918763B","volume":"39","author":"Anastas","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"D2RA05849A\/cit7a\/1","doi-asserted-by":"crossref","first-page":"3805","DOI":"10.1021\/cr100004p","volume":"110","author":"Sridharan","year":"2010","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit7b\/1","doi-asserted-by":"crossref","first-page":"1861","DOI":"10.1021\/cr068408n","volume":"107","author":"Nair","year":"2007","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit7c\/1","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1021\/ar030002z","volume":"37","author":"Nair","year":"2004","journal-title":"Acc. Chem. Res."},{"key":"D2RA05849A\/cit7d\/1","doi-asserted-by":"crossref","first-page":"6851","DOI":"10.1016\/j.tetlet.2006.07.070","volume":"47","author":"Shanmugam","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"D2RA05849A\/cit7e\/1","doi-asserted-by":"crossref","first-page":"591","DOI":"10.1139\/V09-020","volume":"87","author":"Shanmugam","year":"2009","journal-title":"Can. J. Chem."},{"key":"D2RA05849A\/cit8a\/1","doi-asserted-by":"crossref","first-page":"3857","DOI":"10.1016\/0040-4039(96)00699-5","volume":"37","author":"Darses","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"D2RA05849A\/cit8b\/1","doi-asserted-by":"crossref","first-page":"12418","DOI":"10.1021\/jacs.7b07687","volume":"139","author":"Chen","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"D2RA05849A\/cit8c\/1","doi-asserted-by":"crossref","first-page":"2989","DOI":"10.1021\/acscatal.8b00341","volume":"8","author":"Chen","year":"2018","journal-title":"ACS Catal."},{"key":"D2RA05849A\/cit8d\/1","doi-asserted-by":"crossref","first-page":"7007","DOI":"10.1002\/anie.202014842","volume":"60","author":"Sanhueza","year":"2021","journal-title":"Angew. Chem., Int. Ed."},{"key":"D2RA05849A\/cit9\/1","doi-asserted-by":"crossref","first-page":"3636","DOI":"10.1021\/acs.jmedchem.6b01593","volume":"60","author":"Pillaiyar","year":"2017","journal-title":"J. Med. Chem."},{"key":"D2RA05849A\/cit11\/1","doi-asserted-by":"crossref","first-page":"539","DOI":"10.1002\/adsc.201500874","volume":"358","author":"Pu","year":"2016","journal-title":"Adv. Synth. Catal."},{"key":"D2RA05849A\/cit12a\/1","doi-asserted-by":"crossref","first-page":"1189","DOI":"10.1002\/chem.201203354","volume":"19","author":"Ma","year":"2013","journal-title":"Chem.\u2013Eur. J."},{"key":"D2RA05849A\/cit12b\/1","doi-asserted-by":"crossref","first-page":"4602","DOI":"10.1039\/C4OB00714J","volume":"12","author":"Shen","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"D2RA05849A\/cit12c\/1","doi-asserted-by":"crossref","first-page":"4197","DOI":"10.1021\/acs.orglett.2c01484","volume":"24","author":"Zheng","year":"2022","journal-title":"Org. Lett."},{"key":"D2RA05849A\/cit12d\/1","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1016\/j.tet.2014.11.024","volume":"71","author":"Kotha","year":"2015","journal-title":"Tetrahedron"},{"key":"D2RA05849A\/cit12e\/1","doi-asserted-by":"crossref","first-page":"3636","DOI":"10.1021\/acs.jmedchem.6b01593","volume":"60","author":"Pillaiyar","year":"2017","journal-title":"J. Med. Chem."},{"key":"D2RA05849A\/cit12f\/1","doi-asserted-by":"crossref","first-page":"4753","DOI":"10.1021\/jo200561f","volume":"76","author":"Guchhait","year":"2011","journal-title":"J. Org. Chem."},{"key":"D2RA05849A\/cit12g\/1","doi-asserted-by":"crossref","first-page":"151651","DOI":"10.1016\/j.tetlet.2020.151651","volume":"61","author":"Neupane","year":"2020","journal-title":"Tetrahedron Lett."},{"key":"D2RA05849A\/cit12h\/1","doi-asserted-by":"crossref","first-page":"7198","DOI":"10.1016\/j.tetlet.2014.11.009","volume":"55","author":"Das","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"D2RA05849A\/cit13a\/1","doi-asserted-by":"crossref","first-page":"2271","DOI":"10.1016\/j.tetlet.2007.01.172","volume":"48","author":"Khan","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"D2RA05849A\/cit13b\/1","doi-asserted-by":"crossref","first-page":"484","DOI":"10.1039\/C2DT31844J","volume":"42","author":"Shi","year":"2013","journal-title":"Dalton Trans."},{"key":"D2RA05849A\/cit13c\/1","doi-asserted-by":"crossref","first-page":"10205","DOI":"10.3390\/molecules200610205","volume":"20","author":"M\u0142ochowski","year":"2015","journal-title":"Molecules"},{"key":"D2RA05849A\/cit13d\/1","doi-asserted-by":"crossref","first-page":"15438","DOI":"10.1039\/C5CC05713B","volume":"51","author":"Chebolu","year":"2015","journal-title":"Chem. Commun."},{"key":"D2RA05849A\/cit13e\/1","doi-asserted-by":"crossref","first-page":"2119","DOI":"10.1016\/j.tetlet.2008.01.119","volume":"49","author":"Shanmugam","year":"2008","journal-title":"Tetrahedron Lett."},{"key":"D2RA05849A\/cit15a\/1","doi-asserted-by":"crossref","first-page":"6766","DOI":"10.1039\/C6CS00220J","volume":"45","author":"Lopez","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"D2RA05849A\/cit15b\/1","doi-asserted-by":"crossref","first-page":"1300","DOI":"10.1002\/anie.201711602","volume":"57","author":"Ni","year":"2018","journal-title":"Angew. Chem., Int. Ed."},{"key":"D2RA05849A\/cit15c\/1","doi-asserted-by":"crossref","first-page":"S2051","DOI":"10.1016\/j.arabjc.2013.07.035","volume":"10","author":"Jain","year":"2017","journal-title":"Arabian J. Chem."},{"key":"D2RA05849A\/cit15d\/1","doi-asserted-by":"crossref","first-page":"10886","DOI":"10.1021\/jp054693n","volume":"109","author":"Wang","year":"2005","journal-title":"J. Phys. Chem. A"},{"key":"D2RA05849A\/cit15e\/1","doi-asserted-by":"crossref","first-page":"1359","DOI":"10.1021\/cr000664r","volume":"102","author":"Hassan","year":"2002","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit15f\/1","doi-asserted-by":"crossref","first-page":"893","DOI":"10.1021\/cr020033s","volume":"103","author":"Horton","year":"2003","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit15g\/1","doi-asserted-by":"crossref","first-page":"3511","DOI":"10.1021\/jo050104y","volume":"70","author":"Tuanli","year":"2005","journal-title":"J. Org. Chem."},{"key":"D2RA05849A\/cit15h\/1","doi-asserted-by":"crossref","first-page":"174","DOI":"10.1016\/j.dyepig.2014.07.011","volume":"113","author":"He","year":"2015","journal-title":"Dyes Pigm."},{"key":"D2RA05849A\/cit15i\/1","doi-asserted-by":"crossref","first-page":"2075","DOI":"10.1021\/jp210764h","volume":"116","author":"Zhang","year":"2012","journal-title":"J. Phys. Chem. B"},{"key":"D2RA05849A\/cit16a\/1","doi-asserted-by":"crossref","first-page":"5384","DOI":"10.1002\/anie.200462661","volume":"44","author":"Bringmann","year":"2005","journal-title":"Angew. Chem., Int. Ed."},{"key":"D2RA05849A\/cit16b\/1","doi-asserted-by":"crossref","first-page":"11239","DOI":"10.1021\/acs.chemrev.5b00136","volume":"115","author":"Kumarasamy","year":"2015","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit16c\/1","doi-asserted-by":"crossref","first-page":"3418","DOI":"10.1039\/C5CS00012B","volume":"44","author":"Wencel-Delord","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"D2RA05849A\/cit16d\/1","doi-asserted-by":"crossref","first-page":"7304","DOI":"10.1021\/cr500671p","volume":"115","author":"Liu","year":"2015","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit16e\/1","doi-asserted-by":"crossref","first-page":"7001","DOI":"10.1021\/cr5005666","volume":"115","author":"Cook","year":"2015","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit16f\/1","doi-asserted-by":"crossref","first-page":"13752","DOI":"10.1021\/acs.chemrev.6b00354","volume":"116","author":"Yashima","year":"2016","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit16g\/1","doi-asserted-by":"crossref","first-page":"8912","DOI":"10.1021\/jacs.6b04501","volume":"138","author":"Yuan","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"D2RA05849A\/cit16h\/1","doi-asserted-by":"crossref","first-page":"234","DOI":"10.1038\/nchem.2173","volume":"7","author":"Qin","year":"2015","journal-title":"Nat. Chem."},{"key":"D2RA05849A\/cit16i\/1","doi-asserted-by":"crossref","first-page":"4528","DOI":"10.1021\/acs.chemrev.6b00731","volume":"117","author":"Bhat","year":"2017","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit16j\/1","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1021\/cr100155e","volume":"111","author":"Bringmann","year":"2011","journal-title":"Chem. Rev."},{"key":"D2RA05849A\/cit17\/1","doi-asserted-by":"crossref","first-page":"900","DOI":"10.1021\/acs.orglett.5b03429","volume":"18","author":"Kannaboina","year":"2016","journal-title":"Org. Lett."},{"key":"D2RA05849A\/cit18\/1","doi-asserted-by":"crossref","first-page":"1453","DOI":"10.3762\/bjoc.17.101","volume":"17","author":"Dudhe","year":"2021","journal-title":"Beilstein J. Org. Chem."},{"key":"D2RA05849A\/cit19\/1","doi-asserted-by":"crossref","first-page":"1102","DOI":"10.1021\/acssensors.8b00083","volume":"3","author":"Shi","year":"2018","journal-title":"ACS Sens."},{"key":"D2RA05849A\/cit20\/1","doi-asserted-by":"crossref","first-page":"150974","DOI":"10.1016\/j.tetlet.2019.150974","volume":"60","author":"Lee","year":"2019","journal-title":"Tetrahedron Lett."},{"key":"D2RA05849A\/cit21\/1","doi-asserted-by":"crossref","first-page":"8083","DOI":"10.1039\/D1CC03675K","volume":"57","author":"Takaishi","year":"2021","journal-title":"Chem. Commun."},{"key":"D2RA05849A\/cit22\/1","doi-asserted-by":"crossref","first-page":"2664","DOI":"10.1002\/asia.201800766","volume":"13","author":"Qiao","year":"2018","journal-title":"Chem.\u2013Asian J."},{"key":"D2RA05849A\/cit23\/1","doi-asserted-by":"crossref","first-page":"1779","DOI":"10.1055\/s-2005-869897","volume":"2005","author":"Pradhan","year":"2005","journal-title":"Synthesis"},{"key":"D2RA05849A\/cit24\/1","doi-asserted-by":"crossref","first-page":"2301","DOI":"10.1039\/C3TB21860K","volume":"2","author":"Zheng","year":"2014","journal-title":"J. Mater. Chem. B"}],"container-title":["RSC Advances"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/pubs.rsc.org\/en\/content\/articlepdf\/2022\/RA\/D2RA05849A","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,5]],"date-time":"2026-07-05T18:21:01Z","timestamp":1783275661000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.rsc.org\/ra\/article\/12\/47\/30712-30721\/784477"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022]]},"references-count":82,"journal-issue":{"issue":"47","published-print":{"date-parts":[[2022,10,24]]}},"URL":"https:\/\/doi.org\/10.1039\/d2ra05849a","relation":{},"ISSN":["2046-2069"],"issn-type":[{"value":"2046-2069","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022]]}}}